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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 735894Generated: October 30, 2026

Sodium Azide → Methyl 4-(azidomethyl)-1-naphthoate

https://huagongshe.com/reaction/735894

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium AzideHCID 33557—
Reactant1-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl esterHCID 10333813—
SolventDimethyl SulfoxideHCID 679—
SolventWaterHCID 962—
ProductMethyl 4-(azidomethyl)-1-naphthoateHCID 2076304577%

Reaction Steps

To a solution of methyl 4-(bromomethyl)-1-naphthoate (30 g, 0.107 mol) in anhydrous DMSO (300 mL) was added NaN3 portion wise (14 g, 0.215 mol) at 0° C. and stirred at rt for 16 h. Then the reaction mixture was diluted with water (500 mL), extracted with EtOAc (2×250 mL), washed with water, brine and dried over MgSO4. The solvent was removed under vacuum to give methyl 4-(azidomethyl)-1-naphthoate (20 g, 77%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07592477B2
Source datasetuspto-grants-2009_09
ORD IDord-1603d0d10eef4ff58108e96f77f08116
Source noteuspto-grants-2009_09